Title: Southwest Side Cottages | Expedia.ca [Southwest Side Travel Guide](https://expedia.ca/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.ca/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Vacation Rentals in Southwest Side](https://expedia.ca/Southwest-Side-Vacation-Rentals.d553248635976475403.Travel-Guide-VacationRentals)[Flights to Southwest Side](https://expedia.ca/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Side.d553248635976475403.Car-Rental-Guide)[Southwest Side Vacation Packages](https://expedia.ca/Southwest-Side.d553248635976475403.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Southwest Side Cottage Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southwest Side Cottages ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/99000000/98550000/98544600/98544584/12def7ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98550000/98544600/98544584/e50cac73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98550000/98544600/98544584/c734b0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98550000/98544600/98544584/56e92dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Game Nights, Bbqs & Family Fun: Chicago Area Hub Oakton [](https://www.expedia.ca/Chicago-Hotels-Des-Plaines-Vacation-Rental-W-Spacious-Backyard.h98544584.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93548100/93548069/2fab0d87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93548100/93548069/a67ef6ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/94000000/93550000/93548100/93548069/6419b81c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93548100/93548069/342b0679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Classic Oak Park Home, 11 Mi to Downtown Chicago! Oak Park [](https://www.expedia.ca/Chicago-Hotels-Classic-Oak-Park-Home.h93548069.Hotel-Information) ![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/94000000/93610000/93600500/93600477/cd8660e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93610000/93600500/93600477/b6815fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93610000/93600500/93600477/ff2c0954.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93610000/93600500/93600477/7626acad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Westmont Home: Walk to Metra Station! Westmont 2.0/10 (1) "Very upset with the communication of this rental. I booked this rental for a weekend getaway with the family. I received an email a couple of days ahead of the booking reminding me of my trip and that I was all set. Then on check in day, I realized that I needed the check in information. I sent a message through the app to the renter. The response was "it may take a few days for the property to get back with you" so I called the number on the response. The operator then tried to look up my... [](https://www.expedia.ca/Chicago-Hotels-Cozy-Westmont-Home-Walk-To-Metra-Station.h93600477.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94490000/94485900/94485807/c4d10a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94490000/94485900/94485807/bc960a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94490000/94485900/94485807/96aa9693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94490000/94485900/94485807/deea3bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home w/ Office + Yard: 25 Mi to Downtown Chicago! Glen Ellyn [](https://www.expedia.ca/Chicago-Hotels-Home-W-Office-Yard-25-Mi-To-Downtown-Chicago.h94485807.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111920000/111911700/111911602/c37fe511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111920000/111911700/111911602/44ece33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111920000/111911700/111911602/2c9a9271.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111920000/111911700/111911602/dbc3d853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home w/ Fenced Yard: 13 Mi to Downtown Chicago! South Evanston [](https://www.expedia.ca/Chicago-Hotels-Home-W-Fenced-Yard-13-Mi-To-Downtown-Chicago.h111911602.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111670000/111666300/111666247/f244451a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111670000/111666300/111666247/e8c4b381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111670000/111666300/111666247/4d8cc223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111670000/111666300/111666247/0bbcc341.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4 Mi to Lake Michigan: East Chicago Home w/ Grill East Chicago [](https://www.expedia.ca/East-Chicago-Hotels-4-Mi-To-Lake-Michigan-East-Chicago-Home-W-Grill.h111666247.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112500000/112496500/112496448/a80a5593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112500000/112496500/112496448/adfdab57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112500000/112496500/112496448/7a7390fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112500000/112496500/112496448/a6a47db6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Mi to Northwestern: Updated Home w/ Game Room! Evanston 10/10 Exceptional (1) "This recently remodeled home was perfect for our family trip. It was immaculate, comfortable, spacious and well appointed. " [](https://www.expedia.ca/Chicago-Hotels-2-Mi-To-Northwestern-Updated-Home-W-Game-Room.h112496448.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/86000000/85860000/85851900/85851866/6df7627f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/86000000/85860000/85851900/85851866/da378a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/86000000/85860000/85851900/85851866/0250a27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/86000000/85860000/85851900/85851866/0c2cb8d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### “The cottage” 2 bedrooms cozy and private home Markham 9.4/10 Exceptional (8) "We were at this location for 13 days while visiting family. It was just what we needed for our stay. Clean and functional, enough amenities for a long stay " [](https://www.expedia.ca/Chicago-Hotels-The-Cottage-2-Bedrooms-Cozy-And-Private-Home.h85851866.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/115000000/114210000/114205100/114205048/9d8c1ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/115000000/114210000/114205100/114205048/ee914838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/115000000/114210000/114205100/114205048/59e1eebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/115000000/114210000/114205100/114205048/22fe2bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Mi to Hard Rock Casino: Charming Home in Gary! Gary [](https://www.expedia.ca/Gary-Hotels-3-Mi-To-Hard-Rock-Casino-Charming-Home-In-Gary.h114205048.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-08&endDate=2025-10-09®ionId=553248635976475403&adults=2&lodging=COTTAGE&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Cottages.d553248635976475403-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Cottages.d553248635976475403-aaCottages.Travel-Guide-Accommodation) ## Top Southwest Side Hotel Reviews ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Good room. Good location to train. Area is a little suspect" [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![The Chicago Hotel Collection - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143_y.jpg) ### The Chicago Hotel Collection - Magnificent Mile 10/10 Excellent "I loved this hotel, I really enjoyed staying there, it was a very convenient area it's close to everything. I would definitely stay there again. Thank you" [](https://expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![Hyatt Regency Chicago](//images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "perfect" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "We really enjoyed staying at the Whitehall during our Chicago visit. From the moment we stepped in, we were warmly welcomed by the staff. The room was large,clean,and the air conditioning worked great. The breakfast area was lovely and had plenty of great varieties to choose from. The location was top notch and on a quieter street. My only complaint is that the wifi connection is poor. We will likely stay again." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "This is my third time at this hotel . Staff are so nice . Front of house, Jordan’s attention to detail in assisting me with a special request while i was here was next level . I will be back . " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Hilton Chicago](//images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "I thoroughly enjoyed my stay at the Chicago Hilton. Loved the ambiance and the inspiring architecture on entering and the old fashioned elevator lobby was a treat itself. The Irish Pub was outstanding with a nice atmosphere and not overly sports oriented like some. I was there during some kind of trade event but the place never felt crowded or had long waits for anything. My room on the 18th floor was a little spartan for my liking, though quite large, however for the amount spent I expected more. Had a nice view and was quiet enough so I’m not taking points away, but yes - a room update is past due if other rooms were like mine. " [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![River Hotel](//images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg) ### River Hotel 10/10 Excellent "Perfect for a quick weekend trip! " [](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "The hotel was clean, staff was friendly and helpful and great location to get to everything. I would definitely stay there again. This my 7th time ive been to" [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![The Wade](//images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "It was a great hotel!! The room was awesome and the view from our floor was beautiful. We were so close to Navy Pier which was definitely a plus. " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ## Find out more about Southwest Side ## Southwest Side Cottages information | Number of reviews | 9 | | --- | --- | | Accommodation | 11 Cottages | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [1 Star Hotels in South Englewood](https://www.expedia.ca/1Star-South-Englewood-Chicago-Hotels.s10-n6132433-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Cheap-Hotels.0-n6132347-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Hotels-With-Free-Parking.0-n6132347-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Romantic-Hotel.0-n6132347-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - 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[Downtown Chicago Hotels](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Englewood](https://www.expedia.ca/Englewood-Chicago-Hotels-Cheap-Hotels.0-n101911-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Englewood Hotels](https://www.expedia.ca/Englewood-Chicago-Hotels.0-n101911-0.Travel-Guide-Filter-Hotels) - [Apartments in Far Southwest Side](https://www.expedia.ca/Far-Southwest-Side-Apartments.d553248635976475353-aaApartments.Travel-Guide-Accommodation) - [Condo Rentals in Far Southwest Side](https://www.expedia.ca/Far-Southwest-Side-Condos.d553248635976475353-aaCondos.Travel-Guide-Accommodation) - [All Inclusive Resorts and in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-All-Inclusive-Hotel.0-n6132375-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-Business-Hotel.0-n6132375-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-Cheap-Hotels.0-n6132375-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-Luxury-Hotel.0-n6132375-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Gage Park Hotels](https://www.expedia.ca/Gage-Park-Chicago-Hotels.0-n6132375-0.Travel-Guide-Filter-Hotels) - [Hotels near Garfield Station](https://www.expedia.ca/Garfield-Station-Hotels.d6210926.Travel-Guide-Hotels) - [Inns in Garfield Station](https://www.expedia.ca/Garfield-Station-Inns.d6210926-aaInns.Travel-Guide-Accommodation) - [Motel 6 Hotels in Glendale](https://www.expedia.ca/Glendale-Chicago-Hotels-Motel-6.0-n6132385-0--bMotel6.Travel-Guide-Filter-Hotels) - [B&B in Halsted Station](https://www.expedia.ca/Halsted-Station-Bed-And-Breakfast.d6211063-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Halsted Station](https://www.expedia.ca/Halsted-Station-Hotels.d6211063.Travel-Guide-Hotels) - [Vacation Homes in Indiana Station](https://www.expedia.ca/Indiana-Station-Private-Vacation-Homes.d6211032-aaPrivateVacationHomes.Travel-Guide-Accommodation) - 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[Book Cottages in Southwest Side on Expedia.com](https://www.expedia.com/Southwest-Side-Cottages.d553248635976475403-aaCottages.Travel-Guide-Accommodation)